1-Butanol → HCID 136141722, compound

HRID 720149Notes

Reaction equation

HRID 720149 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:30])[NH:14][C:15]1[CH:16]=[C:17]2[C:28](=[O:29])[NH:27][N:26]=[CH:25][C:19]3=[C:20](Cl)[NH:21][C:22]([CH:23]=1)=[C:18]23)([CH3:11])([CH3:10])[CH3:9].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(O)CCC>CO>[C:8]([O:12][C:13](=[O:30])[NH:14][C:15]1[CH:16]=[C:17]2[C:28](=[O:29])[NH:27][N:26]=[CH:25][C:19]3=[C:20]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[NH:21][C:22]([CH:23]=1)=[C:18]23)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8083MorpholineHCID 8471TriethylamineHCID 136141735HCID 136141735, compound

Product 1

HCID 136141722HCID 136141722, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.039 mL, 0.28 mmol), the title compound of Example 187 (46 mg, 0.14 mmol), morpholine (96 mg, 1.1 mmol) and n-butanol (5 mL) were stirred in a flask with a condenser at 120° C. overnight. The mixture was allowed to stand at room temperature for two more days. The volatile components were removed under vacuum and the resulting mixture was subjected to silica gel chromatography, eluting with 95:5 dichloromethane:methanol to afford the title compound (12.5 mg, 0.032 mmol) as a yellow solid in 23% yield.

Workup

  1. customto stand at room temperature for two more days
  2. customThe volatile components were removed under vacuum
  3. washeluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-9111fe2053fe40b398bd2a8653fb3256
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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